Hydrochloric Acid → HCID 178447846, compound

HRID 1975247Notes

Reaction equation

HRID 1975247 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[F:13])(=O)[CH:2]=[CH2:3].[CH2:14]([C@H:17]1[CH2:22][CH2:21][C@H:20]([CH:23]=[CH:24][N:25]2CCCCC2)[CH2:19][CH2:18]1)[CH2:15][CH3:16].Cl.NO.Cl>O.C(O)C>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:1]2[CH:2]=[CH:3][C:23]([C@H:20]3[CH2:21][CH2:22][C@H:17]([CH2:14][CH2:15][CH3:16])[CH2:18][CH2:19]3)=[CH:24][N:25]=2)=[C:6]([F:13])[CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 19101129HCID 19101129, compoundHCID 178447991HCID 178447991, compound

Product 1

HCID 178447846HCID 178447846, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.03 mol of 1-acrylyl-2-fluoro-4-methoxybenzene was mixed at 0° C. with 0.03 mol of 1-[2-(trans-4-propylcyclohexyl)vinyl]piperidine and held at room temperature for 2 hours. The mixture was then treated with 90 ml of ethanol, 10 ml of water, 0.14 mol of hydroxylamine hydrochloride and 1 ml of concentrated hydrochloric acid and heated to reflux for 8 hours. Subsequently, about 2/3 of the solvent were removed by distillation. The concentrated mixture was diluted with 150 ml of water and adjusted to pH 8 with aqueous sodium carbonate solution. The organic layer was extracted with benzene. The extract was washed neutral with water, dried over sodium sulfate, filtered and concentrated. Chromatographic purification of the resulting residue on silica gel with benzene/hexane (vol. 1:1) gave 2-(4-methoxy-2-fluorophenyl)-5-(trans-4-propylcyclohexyl)pyridine in 20% yield; m.p. (C-N) 56.3° C., cl.p. (N-I) 180.6° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 8 hours
  3. customSubsequently, about 2/3 of the solvent were removed by distillation
  4. additionThe concentrated mixture was diluted with 150 ml of water
  5. extractionThe organic layer was extracted with benzene
  6. washThe extract was washed neutral with water
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customChromatographic purification of the resulting residue on silica gel with benzene/hexane (vol. 1:1)

Sources & evidence

ORD record
ord-2bd43a2a7cef45e789b889cc52342548
Source dataset
uspto-grants-1994_02
Patent number
US05284956

Reaction notes

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